The Chemistry of Aromatic Azapentalenes

Elguero, José; Claramunt, R. M.; Summers, A. J. H.

doi:10.1016/s0065-2725(08)60105-1

Cited by 63 publications

(19 citation statements)

References 327 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The problem of the structure and aromaticity of heteropentalenes [92] was examined using NICS as an analytical tool, so we will use this series of compounds to illustrate our approach. These compounds result formally by replacing C atoms of the pentalene dianion 47 by heteroatoms X and Y (Scheme 2.6).…”

Section: Nics and Aromaticitymentioning

confidence: 99%

Computational NMR Spectroscopy

Alkorta

Elguero

2010

Computational Spectroscopy

View full text Add to dashboard Cite

Section: Nics and Aromaticitymentioning

confidence: 99%

Computational NMR Spectroscopy

Alkorta

Elguero

2010

Computational Spectroscopy

View full text Add to dashboard Cite

“…Les charges nettes ne (solvant : DMSO-d6). (10,2,8,4) Les dCriv6s nitr6s synthktisgs sont des substances colorkes caractgriskes par des points de fusion kleves, trss peu solubles en milieu acide et dans les solvants oyganiques usuels. Ces compos6s prdsentent une fluorescence verte en solution dans l'acktone ou dans le chloroforme.…”

Section: I'siunclassified

Synthese et Reactivite du [3, 2‐b] Pyridino [4, 5] Benzo‐1, 3a, 6, 6a‐Tetraazapentalene

Maquestiau

Flammang-Barbieux

Vilain

et al. 1983

Bulletin des Soc Chimique

View full text Add to dashboard Cite

Bull. Soc. Chim. B e l q . vo1.92/nn 1/1983 SYNTHESE ET REACTIVITE DU [9,2-b] PYRIDINO [ 4 , 5 1 BENZO-l,3a,6,6a-TETRAAZAPENTALENE. A. MAQUESTIAU, M. FLAMMANG-BARBIEUX et E. VILAIN. Laboaatoihe de Chimie Ohganique, hiVehbi.t6? d e 1'Eta.t ir Monb. ABSTRACT. A new heteroaromatic pentalene, [3.2-b] pyridino [ 4 , 5 ] benzoil,3a,6,6a-t&traazapentalene [3] has been prepared by direct condensation of 2-chloro-3-ni-tropyridine with benzotriazole followed by reductive cyclisation of the l-(3'n i t r o -2 ' -p y r i d y l ) b e n z o t r i a z o l e intermediate with triethylphosphite. The spectral and chemical properties of this new compound are described and the positions of the introduced substituents are determined a s well by 'H NMR spectroscopy as by EHT calculations.

show abstract

“…[8] The open-ring azidoimine form is favored by electron-withdrawing groups and the tetrazole form is favored in the presence of electron-donating groups. [9] A wide series of fluoroalkyl-substituted imidoazyl azides is known that do not form a tetrazole. [10] A key prerequisite for this cyclization is a cis orientation of the imino lone pair and the azide group.…”

Section: Introductionmentioning

confidence: 99%

Azide–Tetrazole Ring‐Chain Isomerism in Polyazido‐1,3,5‐triazines, Triazido‐s‐heptazine, and Diazidotetrazines

2006

View full text Add to dashboard Cite

The azide-tetrazole isomerism in several polyazido-1,3,5-triazines, triazido-sym-heptazine, and some diazido-1,2,4,5-tetrazines was investigated by ab initio quantum chemical methods in order to determine whether the polyazides are suitable starting materials for the synthesis of the isomeric tetrazoles. The effects of solvation in CCl 4 , DMSO and water on this isomerism were included using the self consistent reaction field (SCRF) method. The effect of amino-and nitrosubstituents on the azide-tetrazole isomerism was also examined. In the gas phase all investigated polyazidoheterocycles do not cyclize to form tetrazoles. An electron-donating amino group favors the ring closure to tetrazoles, whereas an electron-withdrawing nitro group favors the azides. Solvation in polar solvents favors the formation of a tetrazole ring system

show abstract

The Chemistry of Aromatic Azapentalenes

Cited by 63 publications

References 327 publications

Computational NMR Spectroscopy

Computational NMR Spectroscopy

Synthese et Reactivite du [3, 2‐b] Pyridino [4, 5] Benzo‐1, 3a, 6, 6a‐Tetraazapentalene

Azide–Tetrazole Ring‐Chain Isomerism in Polyazido‐1,3,5‐triazines, Triazido‐s‐heptazine, and Diazidotetrazines

Contact Info

Product

Resources

About